This invention relates to novel N-(heterocyclicaminocarbonyl)arylsulfonamides in which at least one of the acyclic nitrogens thereof is substituted by a moiety which may be lower alkyl, or in some cases by methoxy. The compounds of this invention and their agriculturally suitable salts, are useful as agricultural chemicals, such as plant growth regulants and herbicides.
Netherlands Patent No. 121,788, published Sept. 15, 1966, discloses the preparation of compounds of the following Formula and their use as general or selective herbicides, ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sub.2 is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl. PA1 R.sub.2 is H or alkyl of one to three carbon atoms; PA1 R.sub.3 is ##STR10## R.sub.4 and R.sub.7 are independently hydrogen, fluorine, chlorine, bromine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, CF.sub.3 CH.sub.3 S-- or CH.sub.3 CH.sub.2 S; PA1 R.sub.5, R.sub.6 and R.sub.8 are independently hydrogen, fluorine, chlorine, bromine or methyl; PA1 X is Cl, CH.sub.3, --CH.sub.2 CH.sub.3, alkoxy of one to three carbons, CF.sub.3, CH.sub.3 S--, CH.sub.3 OCH.sub.2 -- or CH.sub.3 OCH.sub.2 CH.sub.2 O--; PA1 Y is CH.sub.3 or OCH.sub.3 ; PA1 Z is CH or N; PA1 (a) R.sub.1 and R.sub.2 may not simultaneously be hydrogen; and PA1 (b) when R.sub.4 and R.sub.8 are both hydrogen, at least one of R.sub.5, R.sub.6 or R.sub.7 must be hydrogen; PA1 (c) when R.sub.6 is other than H, at least one or R.sub.4, R.sub.5, R.sub.7 and R.sub.8 is other than H and at least two of R.sub.4, R.sub.5, R.sub.7 and R.sub.8 must be hydrogen; and PA1 (d) when R.sub.6 is H and all of R.sub.4, R.sub.5, R.sub.7 and R.sub.8 are other than H, then all of R.sub.4, R.sub.5, R.sub.7 and R.sub.8 must be either Cl or CH.sub.3. PA1 R.sub.2 is H or alkyl of one to three carbon atoms; PA1 R.sub.3 is ##STR12## R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, CF.sub.3, CH.sub.3 S or CH.sub.3 CH.sub.2 S; PA1 R.sub.4 is R.sub.9 S(O).sub.n ; PA1 R.sub.5, R.sub.6 and R.sub.8 are independently hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA1 R.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, cyclopentyl or cyclopropylmethyl; PA1 X is CH.sub.3, --CH.sub.2 CH.sub.3, alkoxy of one to three carbons, CF.sub.3, CH.sub.3 S--, CH.sub.3 OCH.sub.2 -- or CH.sub.3 OCH.sub.2 CH.sub.2 O--; PA1 Y is CH.sub.3 or OCH.sub.3 ; PA1 Z is CH or N; and PA1 n is 0, 1 or 2; PA1 (a) R.sub.1 and R.sub.2 mat not simultaneously be hydrogen; PA1 (b) when R.sub.6 is other than H, then R.sub.5, R.sub.7 and R.sub.8 must be hydrogen; PA1 (c) when n is 1, then R.sub.7 is other than CH.sub.3 S or CH.sub.3 CH.sub.2 S, and X is other than CH.sub.3 S; PA1 (d) when R.sub.6 is H and R.sub.5, R.sub.7 and R.sub.8 are other than H, then R.sub.5, R.sub.7 and R.sub.8 must either be Cl or CH.sub.3 ; and PA1 (e) when R.sub.9 is C.sub.1 -C.sub.2 alkyl, then n is 1 or 2. PA1 (1) Compounds of the generic scope wherein R.sub.7 is H, Cl, F, Br, CH.sub.3, OCH.sub.3, CF.sub.3 or NO.sub.2, and R.sub.1 is H or CH.sub.3 ; PA1 (2) Compounds of Preferred (1) wherein R.sub.5, R.sub.6 and R.sub.8 are H; PA1 (3) Compounds of Preferred (2) wherein R.sub.2 is H or CH.sub.3 ; PA1 (4) Compounds of Preferred (3) wherein X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or CH.sub.2 OCH.sub.3 ; PA1 (5) Compounds of Preferred (4) wherein R.sub.9 is C.sub.1 -C.sub.4 alkyl and n is 2; PA1 (6) Compounds of Preferred (5) wherein R.sub.7 is H; PA1 (7) Compounds of Preferred (6) wherein R.sub.2 is H and R.sub.1 is CH.sub.3 ; and PA1 (8) Compounds of Preferred (7) wherein R.sub.9 is CH.sub.3. PA1 R.sub.3 is ##STR14## R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, CF.sub.3, CH.sub.3 S or CH.sub.3 CH.sub.2 S; PA1 R.sub.4 is R.sub.9 S(O).sub.n ; PA1 R.sub.5, R.sub.6 and R.sub.8 are independently hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA1 R.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, cyclopentyl or cyclopropylmethyl; PA1 Z is CH or N; PA1 n is 0 or 2; PA1 (a) when R.sub.6 is other than H, then R.sub.5, R.sub.7 and R.sub.8 must be hydrogen; and PA1 (b) when R.sub.6 is H and R.sub.5, R.sub.7 and R.sub.8 are other than H, then R.sub.5, R.sub.7 and R.sub.8 must either be Cl or CH.sub.3.
U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2## wherein R.sub.1 is hydrogen or lower saturated aliphatic acyl; and
The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua.
French Patent No. 1,468,747 discloses the following para-substituted phenylsulfonamides as being useful as antidiabetic agents: ##STR3## wherein R=H, halogen, CF.sub.3 or alkyl.
Compounds of the following formula, and their use as antidiabetic agents, are reported in J. Drug Res. 6, 123 (1974) ##STR4## wherein R is pyridyl.
Logemann et al. Chem Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR5## wherein R is butyl, phenyl or ##STR6## and R.sub.1 is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR7## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
Substituted-pyrimidinyl sulfonylureas of the following formula, which are also para-substituted on the phenyl ring, are disclosed in Farmco Ed. Sci., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959)]: ##STR8## wherein R=H or CH.sub.3.
In EPO application No. 78 3004682, published Apr. 18, 1977, there is taught agricultural compounds of the following formula: ##STR9## wherein R.sub.1 is H, alkyl of one to three carbon atoms or --OCH.sub.3 ;
and their agriculturally suitable salts; provided that:
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing loss of a portion of such valuable crops by killing, or inhibiting the growth or undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. However, the need still exists for effective herbicides that destroy or control weeds while not significantly damaging useful crops. Some weeds (nutsedge is a particular example) are very difficult to control; many of the herbicides that are used to control nutsedge are so nonselective that they cause damage to the crops themselves.